(4-Hydr-oxy-2,5-dimethyl-phen-yl)phenyl-methanone.

The title compound, C(15)H(14)O(2), was obtained by Friedel-Crafts acyl-ation between 2,5-dimethyl-phenol and benzoyl chloride in the presence of aluminium chloride as a catalyst. The dihedral angle between the benzene rings is 61.95 (4)°. In the crystal, O-H⋯O hydrogen bonding and C-H⋯O weak inter-actions lead to polymeric C(6), C(8) and C(11) chains along the a, b and c-axis directions, respectively.

Related literature

For background information on the anti-fungal and anti-inflamatory biological activity of benzophenones, see: Naldoni et al. (2009 ▶); Selvi et al. (2003 ▶); Naveen et al. (2006 ▶). For 104 benzophenone mol­ecules, see: Cox et al. (2008 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C15H14O2

M = 226.26

Orthorhombic,

a = 12.1392 (10) Å

b = 8.1386 (7) Å

c = 23.665 (2) Å

V = 2338.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 123 K

0.25 × 0.12 × 0.05 mm

Data collection

Oxford Diffraction Gemini S diffractometer

Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2009 ▶) T min = 0.904, T max = 1.000

9067 measured reflections

2059 independent reflections

1061 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.058

S = 0.73

2059 reflections

158 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039488/hg2568sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039488/hg2568Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14O2	Dx = 1.286 Mg m−3
Mr = 226.26	Melting point: 443.0(10) K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1709 reflections
a = 12.1392 (10) Å	θ = 2.5–30.7°
b = 8.1386 (7) Å	µ = 0.08 mm−1
c = 23.665 (2) Å	T = 123 K
V = 2338.0 (3) Å3	Shard, colourless
Z = 8	0.25 × 0.12 × 0.05 mm
F(000) = 960

Oxford Diffraction Gemini S diffractometer	2059 independent reflections
Radiation source: fine-focus sealed tube	1061 reflections with I > 2σ(I)
graphite	Rint = 0.061
ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2009)	h = −12→14
Tmin = 0.904, Tmax = 1.000	k = −9→9
9067 measured reflections	l = −28→26

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.058	w = 1/[σ2(Fo2) + (0.0224P)2] where P = (Fo2 + 2Fc2)/3
S = 0.73	(Δ/σ)max < 0.001
2059 reflections	Δρmax = 0.15 e Å−3
158 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (2)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.83004 (8)	0.77322 (14)	0.37654 (5)	0.0301 (3)
O2	0.51698 (9)	0.86337 (14)	0.58360 (5)	0.0261 (3)
H2	0.4559	0.8151	0.5849	0.039*
C1	0.67652 (14)	0.8006 (2)	0.31719 (7)	0.0211 (4)
C2	0.73020 (14)	0.7315 (2)	0.27099 (7)	0.0291 (5)
H2A	0.7986	0.6768	0.2761	0.035*
C3	0.68450 (16)	0.7422 (2)	0.21789 (7)	0.0370 (5)
H3	0.7213	0.6946	0.1865	0.044*
C4	0.58475 (16)	0.8226 (2)	0.21010 (8)	0.0363 (5)
H4	0.5527	0.8278	0.1735	0.044*
C5	0.53206 (15)	0.8948 (2)	0.25549 (7)	0.0306 (5)
H5	0.4649	0.9524	0.2499	0.037*
C6	0.57691 (14)	0.8834 (2)	0.30907 (7)	0.0248 (5)
H6	0.5400	0.9317	0.3403	0.030*
C7	0.72879 (13)	0.78937 (19)	0.37381 (7)	0.0210 (4)
C8	0.66409 (13)	0.80471 (19)	0.42695 (7)	0.0186 (4)
C9	0.71040 (13)	0.9034 (2)	0.46920 (7)	0.0209 (4)
H9	0.7782	0.9572	0.4616	0.025*
C10	0.66178 (13)	0.9261 (2)	0.52152 (7)	0.0185 (4)
C11	0.56262 (13)	0.8428 (2)	0.53126 (7)	0.0195 (4)
C12	0.51675 (13)	0.74203 (19)	0.49063 (7)	0.0210 (4)
H12	0.4505	0.6849	0.4990	0.025*
C13	0.56518 (13)	0.7218 (2)	0.43752 (7)	0.0189 (4)
C14	0.71190 (13)	1.0335 (2)	0.56630 (7)	0.0270 (5)
H14A	0.7342	0.9656	0.5986	0.040*
H14B	0.6577	1.1150	0.5787	0.040*
H14C	0.7766	1.0898	0.5509	0.040*
C15	0.51105 (14)	0.6050 (2)	0.39635 (7)	0.0266 (5)
H15A	0.4730	0.5180	0.4173	0.040*
H15B	0.5673	0.5560	0.3719	0.040*
H15C	0.4577	0.6653	0.3732	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0175 (6)	0.0449 (8)	0.0279 (7)	0.0032 (7)	−0.0010 (6)	0.0015 (7)
O2	0.0221 (7)	0.0330 (8)	0.0231 (7)	−0.0020 (6)	0.0038 (6)	0.0001 (6)
C1	0.0213 (10)	0.0219 (10)	0.0200 (10)	−0.0005 (9)	−0.0006 (9)	0.0020 (9)
C2	0.0321 (10)	0.0282 (12)	0.0269 (11)	0.0059 (9)	0.0025 (10)	0.0014 (9)
C3	0.0531 (13)	0.0374 (13)	0.0206 (11)	0.0084 (11)	0.0015 (11)	−0.0035 (9)
C4	0.0521 (14)	0.0336 (13)	0.0231 (12)	0.0027 (11)	−0.0110 (11)	0.0034 (10)
C5	0.0343 (12)	0.0256 (12)	0.0318 (12)	0.0013 (9)	−0.0102 (10)	0.0043 (10)
C6	0.0256 (10)	0.0246 (11)	0.0241 (11)	−0.0005 (9)	0.0002 (10)	−0.0013 (9)
C7	0.0231 (9)	0.0179 (10)	0.0219 (10)	0.0001 (8)	−0.0003 (9)	0.0007 (9)
C8	0.0176 (9)	0.0187 (10)	0.0196 (10)	0.0029 (8)	−0.0009 (9)	0.0019 (9)
C9	0.0172 (9)	0.0203 (10)	0.0253 (11)	−0.0006 (8)	−0.0015 (9)	0.0069 (9)
C10	0.0199 (10)	0.0173 (10)	0.0185 (10)	0.0035 (8)	−0.0030 (9)	0.0021 (8)
C11	0.0204 (10)	0.0207 (10)	0.0173 (10)	0.0063 (8)	0.0026 (9)	0.0037 (9)
C12	0.0170 (9)	0.0206 (11)	0.0253 (10)	−0.0004 (9)	0.0004 (8)	0.0049 (9)
C13	0.0173 (9)	0.0181 (10)	0.0215 (10)	0.0023 (8)	−0.0029 (8)	0.0006 (8)
C14	0.0252 (10)	0.0274 (11)	0.0283 (11)	−0.0007 (9)	0.0004 (9)	0.0027 (9)
C15	0.0267 (10)	0.0248 (11)	0.0283 (11)	−0.0032 (9)	−0.0006 (9)	−0.0002 (9)

O1—C7	1.2377 (17)	C8—C13	1.400 (2)
O2—C11	1.3674 (18)	C8—C9	1.400 (2)
O2—H2	0.8400	C9—C10	1.384 (2)
C1—C2	1.391 (2)	C9—H9	0.9500
C1—C6	1.397 (2)	C10—C11	1.401 (2)
C1—C7	1.486 (2)	C10—C14	1.503 (2)
C2—C3	1.376 (2)	C11—C12	1.381 (2)
C2—H2A	0.9500	C12—C13	1.397 (2)
C3—C4	1.388 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—C15	1.511 (2)
C4—C5	1.381 (2)	C14—H14A	0.9800
C4—H4	0.9500	C14—H14B	0.9800
C5—C6	1.383 (2)	C14—H14C	0.9800
C5—H5	0.9500	C15—H15A	0.9800
C6—H6	0.9500	C15—H15B	0.9800
C7—C8	1.488 (2)	C15—H15C	0.9800
C11—O2—H2	109.5	C10—C9—H9	118.5
C2—C1—C6	119.48 (15)	C8—C9—H9	118.5
C2—C1—C7	118.93 (15)	C9—C10—C11	116.70 (16)
C6—C1—C7	121.56 (15)	C9—C10—C14	122.40 (15)
C3—C2—C1	120.20 (16)	C11—C10—C14	120.90 (15)
C3—C2—H2A	119.9	O2—C11—C12	122.69 (15)
C1—C2—H2A	119.9	O2—C11—C10	115.98 (15)
C2—C3—C4	120.17 (17)	C12—C11—C10	121.29 (16)
C2—C3—H3	119.9	C11—C12—C13	121.78 (16)
C4—C3—H3	119.9	C11—C12—H12	119.1
C5—C4—C3	120.07 (17)	C13—C12—H12	119.1
C5—C4—H4	120.0	C12—C13—C8	117.69 (15)
C3—C4—H4	120.0	C12—C13—C15	118.11 (15)
C4—C5—C6	120.13 (17)	C8—C13—C15	124.11 (14)
C4—C5—H5	119.9	C10—C14—H14A	109.5
C6—C5—H5	119.9	C10—C14—H14B	109.5
C5—C6—C1	119.93 (16)	H14A—C14—H14B	109.5
C5—C6—H6	120.0	C10—C14—H14C	109.5
C1—C6—H6	120.0	H14A—C14—H14C	109.5
O1—C7—C1	118.54 (16)	H14B—C14—H14C	109.5
O1—C7—C8	119.27 (16)	C13—C15—H15A	109.5
C1—C7—C8	122.12 (14)	C13—C15—H15B	109.5
C13—C8—C9	119.56 (15)	H15A—C15—H15B	109.5
C13—C8—C7	124.28 (15)	C13—C15—H15C	109.5
C9—C8—C7	116.08 (15)	H15A—C15—H15C	109.5
C10—C9—C8	122.95 (16)	H15B—C15—H15C	109.5
C6—C1—C2—C3	−1.1 (3)	C13—C8—C9—C10	−1.2 (2)
C7—C1—C2—C3	−179.02 (16)	C7—C8—C9—C10	−178.15 (15)
C1—C2—C3—C4	0.2 (3)	C8—C9—C10—C11	0.8 (2)
C2—C3—C4—C5	1.3 (3)	C8—C9—C10—C14	−179.48 (16)
C3—C4—C5—C6	−1.8 (3)	C9—C10—C11—O2	178.50 (14)
C4—C5—C6—C1	0.9 (3)	C14—C10—C11—O2	−1.2 (2)
C2—C1—C6—C5	0.5 (3)	C9—C10—C11—C12	0.6 (2)
C7—C1—C6—C5	178.40 (16)	C14—C10—C11—C12	−179.08 (15)
C2—C1—C7—O1	24.8 (2)	O2—C11—C12—C13	−179.51 (14)
C6—C1—C7—O1	−153.09 (16)	C10—C11—C12—C13	−1.8 (2)
C2—C1—C7—C8	−158.14 (16)	C11—C12—C13—C8	1.4 (2)
C6—C1—C7—C8	24.0 (2)	C11—C12—C13—C15	178.17 (14)
O1—C7—C8—C13	−135.69 (17)	C9—C8—C13—C12	0.0 (2)
C1—C7—C8—C13	47.3 (2)	C7—C8—C13—C12	176.75 (15)
O1—C7—C8—C9	41.1 (2)	C9—C8—C13—C15	−176.54 (15)
C1—C7—C8—C9	−135.91 (16)	C7—C8—C13—C15	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.84	1.92	2.6973 (15)	154
C15—H15B···O1ii	0.98	2.62	3.352 (2)	132
C4—H4···O2iii	0.95	2.67	3.454 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.84	1.92	2.6973 (15)	154
C15—H15B⋯O1ii	0.98	2.62	3.352 (2)	132
C4—H4⋯O2iii	0.95	2.67	3.454 (2)	140

Symmetry codes: (i) ; (ii) ; (iii) .